


Helping Hand

by red_crate



Category: Teen Wolf (TV)
Genre: Enthusiastic Consent, First Time, M/M, Sex Toys
Language: English
Status: Completed
Published: 2017-07-26
Updated: 2017-07-26
Packaged: 2018-12-07 09:26:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,682
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11620716
Author URL: https://archiveofourown.org/users/red_crate/pseuds/red_crate
Summary: Stiles can comfort himself with the knowledge that he's not the only guy to ever ask for more than he would face-to-face.Ask for things like help fucking himself on a dildo. He might, however, be the only weirdo lame enough to ask that from someone who isn't his lover, someone he hasn't even kissed.





	Helping Hand

**Author's Note:**

> I decided to explore a couple things here: first time experiences with sex toys, asking a bro to help you out, and, most importantly, consent. Think about Derek's past, and what we can infer that Stiles might have picked up about it (he definitely doesn't know everything).
> 
> My thanks to Twisted_Mind for assuring me this wasn't a completely stupid idea for a fic. <3

 

“Are you sure about this?” Derek's face is earnest as he folds one leg beneath himself on the edge of the bed. The sweatpants he came over in are soft where the fabric brushes Stiles’ leg.

Stiles feels a little ridiculous, but mostly he's still gobsmacked that Derek actually agreed to help him out. Sometimes, Stiles is a little too quick to say exactly what he's thinking, and it is even worse in the middle of the night when he's texting instead of speaking. There are studies on that shit, so at least Stiles can comfort himself with the knowledge that he's not the only guy to ever ask for more than he would face-to-face.

Ask for things like help fucking himself on a dildo. He _might_ , however, be the only weirdo lame enough to ask that from someone who isn't his lover, someone he hasn't even kissed.

“Are you kidding me?” He chuffs, shaking his head. Unbelievable. “I should be asking you that. I mean, _are you sure_? It's, you know, not a normal request.”

Derek shrugs and he puts a hand down on the bed, leaning casually, relaxed. His smile sends heat down Stiles’ face, neck, and chest. “It's a little odd, but I'm actually flattered you asked.” When Stiles smacks a hand over his face, at being reminded that he's so _inexperienced_ , Derek grabs his hand and holds it. “Yeah, I'm sure, Stiles.”

“Okay, good. Because there's no going back from this. Like, I'm naked under here. And you can't unsee that.” Stiles twists a hand in the blanket half strewn across his lap and legs. “You're being really chill about this.”

“I'm sure, Stiles. Relax a little.” Derek squeezes Stiles’ hand before he lets go. “I promise I'm not going to run away screaming. I had a pretty good idea on what to expect when you asked me if I would help you out. I said _yes_.” He slips his fingers under the edge of the blanket where Stiles’ knee is exposed, something like fondness coloring his voice and smile.

Stiles licks his lips, aware of the desire simmering just below the surface. He is gratified when Derek's gaze drops to follow the motion of his tongue. Maybe this isn't going to be completely clinical, like he'd imagined it might be. He takes a deep breath.

“All in, then,” he says, leaning over to his bedside table to slide the drawer open.

He hesitates for just a moment before taking out a half empty bottle of lube and the dildo he bought a while back. The items fall to the bed, and he stares at them. Derek stops him just as he's about to push the blanket off.

“Wait. Here,” he catches Stiles by the back of the neck and tugs him forward, leaning in. His breath fans across Stiles’ face, warm as his eyes.

The kiss is an easy meeting if the lips, not Stiles’ first, but probably the best first kiss he's had yet, despite his nerves. A surprised noise escapes his throat at the unexpected gesture, but Stiles melts into it, grateful for the distraction. When Derek's tongue skims across his lower lip, he lets it inside, meeting him with his own.

“This is going to be fun. Or it's not going to work." Derek pulls away to speak, then tugs his shirt off with one smooth movement. 

He doesn't have a shit-eating grin on his face when he looks back at Stiles, but it's close enough. Derek being playful is still something Stiles is getting used to. Those first few months where Derek was just a brooding and ill-tempered sourwolf kind of left an impression on him. Stiles definitely prefers this slightly more at ease version of Derek.

“Fuck you,” Stiles mutters a little breathy, rolling his eyes for effect. “How are you _real_?”

Stiles knows his cheeks must be doing that ugly, splotchy blush he gets when he's worked up. But honestly, how could anyone expect him to be calm and collected when they've got this guy in their bed, happily lending a hand in sexual endeavors?

He cups Derek's jaw (he's wondered what exactly his beard would feel like for much longer than he's willing to admit) and kisses the smile off Derek's face. Because kissing is apparently on the table now. Hell fucking _yes._  Stiles groans, sucking on Derek's lip, rubbing his thumb along the corner of Derek's jaw just to feel the way it works as they kiss. When Derek shifts closer, pushing the blanket off him, Stiles falls back to the bed with a happy sigh. Definitely not clinical.

Derek runs his hand up Stiles’ thigh without looking at how exposed he is. It sends a shiver down Stiles’ spine. His dick, which had been half hard since Derek knocked on his window, stiffens up all the way. He skims his hand hesitantly down the side of Derek's neck, and when he doesn't get growled at, continues sliding it downward, over his chest. Derek lets him explore, propped up on one elbow where he's leaning over him.

In the close space between them, the reality of what is about to happen hits him. He breaks away, falling down to the bed with an incredulous laugh. He covers his face with one hand, insecurity rushing up all over again.

This was just supposed to be a simple thing. Stiles liked jerking off and, after some exploring, realized a few months ago he liked a finger or two up his ass when he rubbed one out. After that, researching and ordering a modestly sized dildo seemed logical. If he liked a couple fingers, how much better would something more solid and longer feel? Except he'd stalled out every time he tried getting the thing inside. Not because it was too thick or because he didn't prep himself enough.

Stiles has a problem because it feels so _foreign_. Something he has control over, but no sense of connection to. When he imagines using it, he gets hot all over. It turns him on because he already knows how his fingers feel there. However, when it comes to actually sliding it inside, he clenches up and gets sweaty for a whole different reason.

Now, Derek is here and willing to help him out. He doesn't know if having someone else there, someone else in control will make it better or worse. Maybe he just won't be able to use a sex toy on himself. That's probably not the saddest or dumbest thing to ever happen to someone. But he feels stupid, and worries being unable to get into it will make Derek feel bad.

Maybe he hadn't thought through this enough. Of course, when he'd text blurted out his request, he _hadn't_ been thinking. That's the problem.

Derek pushes up on one hand, brows furrowed with concern. “Hey, if you don't want to do this, that's okay.” His other hand rubs at Stiles’ bicep.

The firm way Derek speaks, like he doesn't care if he ended up coming over and kissing him for no reason is perfectly okay, makes Stiles nod his head. It's reassuring even if it feels silly to him. Of course he doesn't have to do this, but the knot in his stomach loosens at Derek's confirmation. It makes him wonder though, not for the first time, what all Derek went through in his past.

“No, I want to. Just...nerves. Ya know.” Stiles pats the bed, blindly looking for the lube. When he finds it, he flicks the lid open with his thumb. “So, here goes nothing.”

He sucks his bottom lip into his mouth, squeezing out enough lubricant to slick his fingers. Stiles focuses on his task, spreading his knees and reaching down to palm his cock a little. His erection hadn't lagged much in the midst of his crisis of confidence, mostly thanks to being a horny teenager. His eyes flutter at the familiar sensation sending sparks of arousal swirling along his skin.

He feels Derek shift on the bed, kneel between where Stiles’ knees are bent and spread. Large, warm hands run up his calves, fingers massaging the muscle in a soothing fashion. Stiles looks up at him from below his lashes and finds Derek staring down at where he's got his cock fisted loosely in hand.

The light flush on Derek's face, just barely visible above his beard, emboldens Stiles to slip his hand further down. Derek’s lips part and his gaze tracks Stiles’ fingers where they tease and circle his hole. It's a thrilling experience, having someone like Derek watching him, maybe even wanting him.

Stiles feels sexy, powerful, in a way he never has before.

It's enough to make the first breach of the tip of one finger an easy slide. He feels hot and tight, but not uncomfortably so. Stiles thinks about what it would be like if Derek asked to press one of his fingers inside along with Stiles’. He has to wrap his other hand around his cock then to relieve the ache already starting to build. A soft puff of air escapes his mouth, arching his hips to push against the second finger while he rubs the palm of his hand over the head of his cock where it's slippery with precome.

Derek’s hands are tight on Stiles’ knees now, not bruising but present nonetheless. He looks strung tense with concentration. It's almost comical, the fact that he has a small little frown between those expressive brows of his. More than that though, Stiles can't get over the way it feels to have all that focus on him, on just _watching_ him.

It isn't long before Stiles has two fingers inside as far as he can get them. Rocking his hips minutely, he spreads them against the clutch of muscle. The stretch is familiar and so good; he tries pushing up enough to find that sweet spot, but only glances close enough to feel desperate for it. He moves his other hand down to massage the thin skin between his sac and hole. The bright twist of _so good, not enough_ pushes a fresh glob of milky liquid out of his cock head.

“Fuck, fuck, okay.” Stiles is panting, legs shaking. “Now, please!” He arches his neck, eyes closed.

He doesn't think he can handle the sight of Derek slicking up the dildo. The sound, wet and visceral, makes Stiles’ cheeks heat even as he fucks his fingers in and out a little roughly. Imagining what the dildo will feel like inside is enough to make Stiles bite his lip with want. The fact that Derek will be the one fucking him with it takes Stiles to a whole other level.

When he speaks next, Derek's voice is husky. “Okay?”

Stiles blinks his eyes open, finding Derek propped up above him. His thick arm is levered next to Stiles’ head as the rest of his body hovers above him. He’s so close, Stiles can't help but think about how easy it would be for him to forgo the dildo and use his own cock. Derek presses his cheek against Stiles’ for a moment, and reaches down to gently tug Stiles’ fingers out.

Stiles doesn't mean to grab Derek's shoulder with his wet fingers, but he has to hold on somehow. They slide over the arch of Derek's trapezius muscles—which, wow, are rock solid and flex under his fingers as he reaches down. Everything feels almost too intense. Derek's quick breathing, warm across his neck, is something to focus on as the blunt tip of the dildo is pressed against his hole. For a second, Stiles tenses up at the intrusion, but Derek nuzzles his ear and lets out a soft groan that makes Stiles practically melt with desire.

“Good,” Derek says as if he's only voicing part of a sentence. His mouth drags along Stiles’ jaw, wet and soft.

Before he knows it, Stiles is taking the the whole head, flare of it catching at his rim in a delicious, dirty tug when Derek pulls the toy back out before pressing it further in. Stiles shudders, full body, at the sting and burn of the silicone spreading him a little further than his fingers had. The pain isn't exactly bad. It underscores the pleasure and fullness he's never had before now.

He moans, bearing down to get more inside. He’s been fantasizing about fucking himself on a dildo for months now. The experience is better than he'd hoped, especially after the handful of failed attempts he'd had so far. Stiles lets go of Derek's shoulder and reaches up to brace his hand against his headboard, using it as leverage to fuck back on the dildo.

Derek makes a sound, something between a growl and a moan, and sits back again. His eyes are dark with desire, Stiles is almost sure of it. The front of his sweatpants is tented, and there's a damp patch that Stiles can't help but stare at. He caused that, didn't he?

“Stiles.” The word is said like a prayer, reverent.

Derek keeps his grip steady on the dildo, and lets Stiles fuck himself on it. They keep it up for a few minutes before Derek angles the toy up and _finally, finally_ Stiles gets a solid stroke against his prostate.

“There, oh fuck. Don't move, please!”

Stiles hasn't taken his free hand off his cock the whole time, but hadn't chanced stroking himself for fear of coming too soon. Now though, he can't stop himself, doesn't want to, from stripping his cock which has been steadily weeping since they began. Derek listens, keeps the angle perfect for him. His balls draw up just before he's clutching his ass around the dildo and spilling hot across his stomach.

It's one of the best orgasms he's ever had.

The aftershocks of his orgasm roll through Stiles, leaving behind a relaxed, sated state. Still, the slide of the dildo being carefully pulled out makes him squirm with sensitivity. His legs collapse back onto the bed, strewn this way and that. He's splayed open and bare in front of Derek, but after what they just did, Stiles can't find it in himself to care right now. He's pretty sure he has the dopiest grin on his face.

Derek sets the dildo to the side, and Stiles will need to remember to clean that later. Then, Derek is stretching out on Stiles' other side. He rests a hand on Stiles’ forearm, but doesn't make any other move.

Brain come-drunk and sloppy, it takes Stiles several long minutes where he nearly dozed off before he thinks to shake some alertness into his head. He looks over at Derek, who is lying there, casually looking him over.

“Hey,” he croaks, mouth dry from all the panting he'd been doing earlier. “Do you, uh...I can…?”

Stiles turns onto his side, wincing at the weird feeling in his ass, almost like he can still feel the dildo inside. He gestures to Derek's crotch, noticing how he's still kind of hard.

Derek squeezes Stiles’ arm. “It's okay. I'm good.” His smile is small, easy. Derek's hazel eyes squint at the edges.

Maybe later he’ll kick himself for not insisting, but right now, Stiles is content to curl his body towards Derek's and bask in the tiny bubble of contentment radiating between the two of them. It's nice, and he can admit that this isn't what he'd ever really pictured for his first non-solo sex act. It's better. Next time he tries the dildo by himself, he'll have this memory to reflect on, relaxed and so good that he can't imagine having trouble with it again.

“Thanks.” Stiles grins and presses his face into the pillow, a little overwhelmed at the relief and happiness he feels.

When he has to come up for air, Derek has moved closer and tucked a hand under his face. He’s still got that soft smile. “You're welcome.”

Stiles giggles at the absurdity of their situation. It's awesome.

 

**Author's Note:**

> I haven't written Sterek in literal years. But here I am again, because Teen Wolf is a black hole. ;) I've missed these two. 
> 
>  
> 
> Check me out on [tumblr](http://the-redcrate.tumblr.com). I ship mostly Sterek and Steter, though I'm a shameless multishipper.


End file.
